Assessing the regioselectivity of oleD-catalyzed glycosylation with a diverse set of acceptors

Maoquan Zhou, Adel Hamza, Chang Guo Zhan, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavonesñY (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2- methoxyestradiol)- were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.

Original languageEnglish
Pages (from-to)279-286
Number of pages8
JournalJournal of Natural Products
Volume76
Issue number2
DOIs
StatePublished - Feb 22 2013

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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